Last October, when I interviewed Portland singer/songwriter Chris Robley, I declared to the man’s face that his song “The Love I Fake” was “one of the best songs I’ve heard about a prostitute.” Robley then cheekily suggested that I had a whole iPod subcategory for prostitute songs. Truth be told, I do not categorize my music library to such a specific degree, but the idea of putting together a “prostitute mix” seemed so funny and obscure that I had to put this mix together. And now, here we have it – 15 songs, obscure and well-known, from jazz to disco to rap to below-the-radar indie artists like Mr. Robley himself. Nearly every kind of musician has something to say about the world’s oldest profession. The inclusion of some of these songs is questionable, I’ll admit... and I'm definitely counting songs about men – all is fair in love and the sex trade. Fire up your preferred electronic music player, and please, for the love of all that is pure, do try to fight that urge to visit your favorite Nevada bunny ranch!

"The Love I Fake," Chris Robley
(The Drunken Dance of Modern Man in Love)
This is the one that started it all. Robley’s tale of a prostitute who creates a sense of empowerment by making fun of her clients is indeed the deepest and most sensitive of the “prostitute” songs here. Not only does she acknowledge the emotional distance required for her to get through the rigors of her chosen profession (“I wish I could feel the love I fake”), she also has quite the noble goal for her hard-earned cash: to “buy back the house” her father lost to foreclosure. Is Daddy proud? We don’t know. But he sure must be grateful that some professions never die.

"The Whores Hustle and the Hustlers Whore," PJ Harvey (Stories of the City, Stories of the Sea)
Prostitutes are a backdrop to, and a source of, stories of the tender underbelly of New York City in this tune by Ms. Polly Jean Harvey. They speak to her of heroin, speed, syphilis, and all those other delicacies of street life. They’re also a metaphor for the well-dressed business people who drive the city’s economy, but we don’t need to get that deep here. The guitars pack a concrete punch that’ll keep you from thinking too hard.

"Just a Gigolo," Thelonious Monk (Misterioso)
The versions by Louis Prima and David Lee Roth are just too obvious, and besides, a little solo jazz piano breather is kind of nice in between two loud rockers. It’s a classic in any form, giving voice to that rare animal known as the male prostitute. They don’t get nearly enough recognition in song.

"He's a Whore," Cheap Trick (Cheap Trick)
…and here’s the other classic gigolo song. When not doling out the cutesy pop of “I Want You to Want Me” and the power balladry of “The Flame,” Cheap Trick has no qualms about rockin’ out with tales of twisted and seedy characters. “He’s a Whore,” from their first album, is one of the best. The male prostitute in this song has no standards. He sees a potential client with “a face that could stop a clock,” but he doesn’t care about her looks: “money’s green, like tea and so is her teeth” – ew! Like a less noble equivalent to the prostitute in “The Love I Fake,” the gigolo in “He’s a Whore” sees his client as “a joke.” But again, this is serious business. And this song seriously rocks. Crank it up!

“Teenage Prostitute,” Frank Zappa (Ship Arriving Too Late to Save a Drowning Witch)
The content is rather simple: girl is a streetwalker, would like to leave the business, but her pimp will give her trouble. Like many Zappa tunes, it’s even more noteworthy for the mind-numbing virtuosity of his band than its subtle-as-a-siren lyrics. Tiny Tim-like falsetto vocals, speedy vibraphone runs, short in length with punk-like intensity… it’s a fast song about a fast life.

"Midnight Caller," Badfinger (No Dice)
Badfinger’s super sensitive Pete Ham wrote this song about a friend of the band’s who turned to prostitution to pay the bills. Word kind of just trickled back to the poor girl’s friends, and by the time Ham found out, he felt really bad that she couldn’t bring herself to ask her friends for a hand. Ham’s plaintive vocal and gorgeous melody are a heart-tugging combination.

"Bad Girls," Donna Summer (Bad Girls)
“Toot toot! Hey, beep beep!” No one knows who they are, but we all know what they do. This is a great example of the wild side of disco, by the queen of the genre herself.

“Wild Thing,” Tone Loc (Loc-ed After Dark)
It’s that line in the last verse that earns this number one rap hit from 1989 its rightful place in the Prostitute Mix: “I need fifty dollars to make you holler / I get paid to do the wild thing!” It was a perfect zinger then, and it still raises a smile now.

"What Do You Do for Money Honey," AC/DC
(Back in Black)
This slice of early ‘80s metal is aimed more at your run-of-the-mill gold digger (“squeezin’ all the blood out of men”), but phrases like “you’re never gonna give it for free” and “lookin’ at your beat on the street” make the implication clear enough. We may still be asking how the subject of this song is employed, but even if she’s got some legitimate income, the evidence shows she’s a hooker in spirit nonetheless.

"Roxanne," the Police (Outlandos d'Amour)
This all-time classic reveals more about the guy singing to the prostitute than the object of his affection. He wants to save her (“you don’t have to sell your body to the night”) and is actually in love with her (“I won’t share you with another boy”). I hope he has another job lined up for her, because love ain’t gonna be enough in this case. Maybe give her a cut of the songwriter’s royalties, perhaps?

"XXX," Helium (Pirate Prude EP)
Helium’s debut release for the Matador label contained this plodding, fuzzed-out gem, written from the perspective of a whore who’s apparently on the verge of a breakdown. She’s standing on the corner, ready to get into a john’s car, but there’s a catch (which, cleverly, also happens to be the song’s hook). His money won’t be adequate payment after all. “You’re gonna pay me with your life.” Run away!

"Rider," Juliana Hatfield (I See You EP)
This raging Hatfield rocker is really about shameless groupies who degrade themselves just to get near their idols (“aims only to please / always on her knees”). But like AC/DC, Hatfield doesn’t mince words: “Is there any blood left in you / Or are you really just a whore?” Going so far as to repeat the “w” word seven times at the end of the song, almost like a chant, the last one carries on to the end of the song in a Joan Jett-like rasp of anger.

"The Kids," Lou Reed (Berlin)
This is another of the “questionable” entries, but the horrible mother of which Lou Reed sings could have been receiving payment for all the “sisters and brothers” she was getting’ it on with. After all, merely being promiscuous isn’t enough to have the authorities take your kids away. And by the way, those are producer Bob Ezrin’s kids screaming “Mommy!” about 5 minutes in.

"Love For Sale," Ella Fitzgerald (The Best of the Songbooks)
Lots of folks have covered this Cole Porter classic. Ella owns it. The way she sings this song, one would think that going into the sex trade might actually be kind of glamorous. That was Ella’s gift – no one else could add this much class to a prostitute song.

"Christmas Card from a Hooker in Minneapolis," Tom Waits (Blue Valentines)We now head back to the piano lounge for the last round…The hooker to which gravelly Tom Waits gives voice is apparently changing her ways. Pregnant, sobering up, getting back in touch with her parents…but still in some trouble. And this is Waits’ gift – he can sing about the heavy aspects of street life and still keep it light. Who knew prostitutes even bothered to send out Christmas cards?